I Am Trying To Break Your Heart Synopsis

A chronicle which follows alternative-country-turned-rock-band Wilco's recording of their fourth album, "Yankee Hotel Foxtrot" (the album was released to critical acclaim by Nonesuch Records). Initially intended to follow the collaborative process of this handful of very creative artists making a highly anticipated album, director Sam Jones soon had unexpected human drama and corporate intrigue to contend with when the band started breaking apart and their now-acclaimed new album was rejected by their label, Reprise Records.

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I Am Trying To Break Your Heart Casts

Fred Armisen
Fred Armisen

Himself

Greg Kot
Greg Kot

Himself

Jeff Tweedy
Jeff Tweedy

Himself

Wes Orshoski
Wes Orshoski

Himself

Leroy Bach
Leroy Bach

Himself